Reaction #696715

ord-c7267f3cc8c946ed98d5f1e165c74990

Reaction equation

Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O
5'-O-tert-butyldiphenylsilyl-2'-O-[N,N-dimethylaminooxyethyl]-5-methyluridine
CCN(CC)CC.F.F.F
Triethylamine trihydrofluoride
CCN(CC)CC
triethylamine
CO
MeOH
→
Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O
2'-O-(dimethylaminooxyethyl)-5-methyluridine
Yield 92.5%

Reactants

Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O
5'-O-tert-butyldiphenylsilyl-2'-O-[N,N-dimethylaminooxyethyl]-5-methyluridine
CCN(CC)CC.F.F.F
Triethylamine trihydrofluoride
CCN(CC)CC
triethylamine
CO
MeOH
—
triethylamine-2HF

Reagents

None

Solvents

ClCCl
CH2Cl2
C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherReaction
  2. 2
    OtherSolvent was removed under vacuum
  3. 3
    Washeluted with 10% MeOH in CH2Cl2

Procedure

Triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) was dissolved in dry THF and triethylamine (1.67 mL, 12 mmol, dry, kept over KOH). This mixture of triethylamine-2HF was then added to 5'-O-tert-butyldiphenylsilyl-2'-O-[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol) and stirred at room temperature for 24 hrs. Reaction was monitored by TLC (5% MeOH in CH2Cl2). Solvent was removed under vacuum and the residue placed on a flash column and eluted with 10% MeOH in CH2Cl2 to get 2'-O-(dimethylaminooxyethyl)-5-methyluridine (766 mg, 92.5%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05998148uspto-grants-1999_12